In a boardroom on the 26th floor of Trump Tower, in a meeting in the late 1980s in the offices of the Trump Organization, one of Donald Trump’s deputies had had it. Blanche Sprague earlier in the day had learned of the death of a friend in a car wreck, and Trump was berating one of the people seated at the conference table, and so Sprague angrily stood up. “It just became too much,” she said the other day on the phone from New York, “and I said, ‘I can’t take it anymore,’ and I just walked out.”

She regretted it immediately, thinking surely Trump would fire her. Then her phone rang. It was him. She told him she wanted to write letters of apology to the 20 or so people at the meeting.

Story Continued Below

Don’t, Trump said.

“He said, ‘No, that would hurt you, possibly change you—I don’t want you to do it,’” Sprague said. “He didn’t want to put me in a position of having to be weakened by my mistake.”

Over these last 40 lime-lighted years, Trump has won a lot, but he has lost a lot, too—four corporate bankruptcies, two failed marriages and a vast array of money-squandering business ventures. He lost his signature Trump Shuttle airline to his lenders. His self-branded casinos in Atlantic City struggled consistently to turn profits. In each case, though, he has heeded a form of the advice he gave that day to Sprague: Never acknowledge failure. Never admit defeat.

On Monday, after months of denouncing rivals and critics as “losers,” the man who has promised “so much winning” America “will get bored with winning” and who has broken every conventional campaign rule on his improbable rise to the top of the GOP field will face his first real electoral test. Finally, there will be quantifiable results. Though the latest polls suggest otherwise, Trump might lose. And if it doesn’t happen in Iowa, maybe it will in New Hampshire, or South Carolina, or Nevada, or in any of the many primaries to come over the next frenzied few months. And if that happens?

He will deny and distort and belittle his critics and change the subject.

He will say that he won.

He always has.

“He’s probably the greatest self-promoter and self-spinmeister that’s ever lived,” said Harry Hurt III, the author of Lost Tycoon: The Many Lives of Donald J. Trump. “By claiming victory over and over again, it starts to become a self-fulfilling prophecy.”

“He’s been able to create his own reality,” said Wayne Barrett, the author of Trump: The Deals and the Downfall.

“It’s admirable in a way, how he defines himself as succeeding where others see failure,” said Michael D’Antonio, the author of Never Enough: Donald Trump and the Pursuit of Success. “It’s a remarkable performance, and one he’s been giving all his life.”

***

“Man is the most vicious of all animals,” Trump told People in 1981, “and life is a series of battles ending in victory or defeat.”

Two years after he said that, he bought the New Jersey Generals of the second-rate United States Football League. It got him in Sports Illustrated and on the back page of the New York City tabloids, adding considerably to his fledgling celebrity. Eager to challenge the National Football League, he wanted the USFL to shift its schedule from the spring to the fall. Most of his fellow owners didn’t want that. TV networks weren’t interested in putting the USFL up against the better quality NFL. Trump sued the NFL and its commissioner, saying the NFL was a monopoly, seeking more than $1 billion in damages. Jurors ruled that the NFL essentially was a monopoly but that the USFL was the cause of its own problems. The NFL was ordered to write a check to the USFL … for $3.76. USFL owners had lost more than $150 million. Trump had lost $22 million. The USFL folded in 1986. Many people blamed Trump.

Trump?

“The sports business is a lousy business,” he told Playboy.

Years later, in an interview with the Buffalo News, he drastically underplayed his role in the decisions that led to the USFL’s demise. “That wasn’t a Trump thing,” he said.

In the late ‘80s, he went on a shopping jag, overpaying for properties with hundreds of millions of dollars borrowed from banks.

He bought for $29-million a 282-foot yacht, which could sleep 52 staff and came with gold doorknobs and a sundeck protected by bulletproof glass. He used it primarily as a trophy. “I’m not even interested in boats,” he told the Chicago Tribune.

He took out a $425 million loan, personally guaranteeing $125 million of it, to buy the Plaza hotel in Manhattan for $407.5 million—the most money ever paid for a hotel—without even doing a careful inspection, according to Gwenda Blair in her book The Trumps. He bought the space for a full-page open letter in the New York Times. “For the first time in my life, I have knowingly made a deal that was not economic—for I can never justify the price I paid, no matter how successful the Plaza becomes.” He said he had purchased “a masterpiece—the Mona Lisa.”

He took out a $400 million loan, personally guaranteeing $100 million of that, to buy the Eastern Air Shuttle for $365 million—even though the company itself had just valued the shuttle at $300 million. Talking to reporters, he compared this, too, to the Mona Lisa. He wanted to decorate the insides of the planes with marble before being told that would make them too heavy to fly.

In 1990, he opened his third casino in Atlantic City, New Jersey—the Trump Taj Mahal joined the Trump Plaza and the Trump Castle—and the launch was chaotic, with underprepared, overburdened staff and malfunctioning slot machines. Trump went on CNN and told Larry King his casino was doing so poorly because his casino was doing so well. The machines, he suggested, simply couldn’t keep up with the demand.

“It would be, like, too much use?” King asked.

“They were virtually on fire,” Trump answered.

But soon it was clear: Trump was more than $3 billion in debt, $900 million of which he had personally guaranteed, and his casinos were struggling, in a city that was struggling, in an economy that was struggling. Trump blamed it on the recession. He blamed it on the invasion of Kuwait by Saddam Hussein, “that madman.” He blamed his employees. In the New York Times, he denigrated the president of one of his casinos, calling him “a Type C personality,” and he said he also was “upset with the people running the Trump Shuttle.” He said the press was “dishonest.” He said people were “jealous.”

Trump’s marriage was crumbling, too, due in part to his infidelity—this was the first of his divorces—but he saw it at least as a publicity victory because the high-profile unraveling made him and his name fixtures on the fronts of well-read tabloids.

“This is great for business,” Trump told John O’Donnell, a president of one of his casinos—not the one with the “Type C personality”—according to a book he wrote later called Trumped! “The way this works is, this’ll bring all the men in,” O’Donnell said Trump told him. “They’re going to want to be with Trump.”

O’Donnell wrote the book after he quit working for Trump. In it, he portrayed Trump as an intemperate, incompetent, self-centered racist. O’Donnell, Trump said, was “a fucking loser.”

In late 1990, in Palm Beach, Florida, banks forced him to hold an auction to get rid of empty, unsold condos in a building of his. Embarrassing? “You know what I think?” he said. “I think there’s something very sophisticated and intelligent about auctions.”

He slipped off the Forbes list of the 400 richest people in the country. After years of angling for higher positions in the rankings—he “constantly calls,” an editor of the magazine told Tim O’Brien for his book, TrumpNation—Trump trashed the publication, calling it “sloppy” and “arbitrary.”

Ultimately, though, the banks gave Trump a break, because they were as tethered to him as he was to them. Trump lost control of the Plaza and the Shuttle—he sold the yacht to a Saudi royal—but the banks loaned him $65 million. They deferred all his payments for three to five years. They put him on an allowance—of $450,000 a month. “It’s a good deal,” Trump told Fortune. In a book he co-wrote that came out that year, titled Surviving at the Top, he said it was “a great victory.”

He also in the book recounted a recent trip to West Point, where he had been “strolling the grounds while talking with some military men,” at which point he came upon a statue of General Douglas MacArthur. He read the inscription of something MacArthur had said: “Your mission remains fixed, determined, inviolable. It is to win wars.”

This made Trump think of himself.

“Just win wars,” he wrote in the book. “The general was talking to soldiers, of course, but I felt that what he said applied to me as well. My main purpose in life is to keep winning.”

***

The Trump Taj Mahal went bankrupt in 1991.

The Trump Castle and the Trump Plaza went bankrupt in 1992.

Thanks, though, to the gilded, too-big-to-fail reprieve Trump had gotten from the banks, and then loans from his siblings from their inheritances from their father, who had made hundreds of millions of dollars building apartments and homes for middle-class families in Brooklyn and Queens, Trump managed to avoid personal bankruptcy.

He then took his casinos public in the mid-1990s, transferring their debt, hundreds of millions of dollars, to shareholders. He declared it to be “a very good deal.”